Prodigiosin metabolites of a marine Pseudomonas species

Gandhi, N. M.; Patell, J. R.; Gandhi, Jagruti P.; Souza, N. J. De; Köhl, H.

doi:10.1007/bf00388799

Cited by 25 publications

(29 citation statements)

References 13 publications

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“…Compound 2 had previously not been isolated, although its existence had been suggested on the basis of TLC and MS 2. Subsequent LC-MS/MS studies had further supported the proposed structure 3.…”

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confidence: 97%

A 2-Substituted Prodiginine, 2-(p-Hydroxybenzyl)prodigiosin, from Pseudoalteromonas rubra

et al. 2008

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In the course of work aimed at the discovery of new pharmaceutical lead compounds from marine bacteria, a lipophilic extract of the bacterium Pseudoalteromonas rubra displayed significant cytotoxicity against SKOV-3, a human ovarian adenocarcinoma cell line. Bioassay-directed fractionation of this extract resulted in the isolation of a series of known and new prodiginine-type azafulvenes. The structure of the major metabolite was elucidated by interpretation of spectroscopic data as a 2-substituted prodigiosin, which we named 2-(phydroxybenzyl)prodigiosin (HBPG).As part of a screening program aimed at the discovery of new lead compounds for the treatment of infective and neoplastic diseases, we isolated a bacterium from the surface of a nudibranch recovered by SCUBA in waters off Oahu, Hawaii, and from a sponge, Mycale armata, collected in shallow waters. Both isolates were shown to be Pseudoalteromonas rubra on the basis of sequence of the 16S rDNA ITS linker gene sequence. Extracts of this bacterium grown in marine broth consistently displayed broad spectrum biological activity against Escherichia coli (ATCC 25922), Staphylococcus aureus (ATCC 25923), methicillinresistant Staphylococcus aureus (ATCC 43300), Candida albicans as well as the human ovarian adenocarcinoma cell line SKOV-3 (ATCC HTB-77). Therefore, this isolate was selected for scale-up and isolation of the active component. A brief optimization study of fermentation conditions indicated that agitation of the culture was detrimental and that a large surface to volume ratio was beneficial to production of the active component. The active principle was located in both the cell pellet and the medium. After extraction with a 2:3 mixture of acetone/Et 2 O, a combination of silica-gel flash chromatography and RP-HPLC yielded 1 in 1.3 % yield based on dry extract mass.The active principle was isolated as a dark red, optically inactive solid. The molecular formula was established by high-resolution positive ion APCI-TOF MS in conjunction with 1 H and 13 C NMR spectroscopic data. A pseudomolecular [M+H] + ion was observed at m/z = 430.2489, consistent with a molecular formula of C 27 H 32 N 3 O 2 (calc. 430.2489, Δ = 0.0 ppm). Support for this molecular formula came from the analysis of 13 C NMR and HSQC spectra recorded in CDCl 3 , which revealed the presence of 25 carbon resonances, comprising resonances for three methyl, five methylene, seven methine and ten quaternary

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confidence: 97%

A 2-Substituted Prodiginine, 2-(p-Hydroxybenzyl)prodigiosin, from Pseudoalteromonas rubra

et al. 2008

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“…106 The bacterial source of these compounds, Pseudomonas magniorubra , was obtained through washings of the marine alga Caulerpa peltata collected near Mumbai, India. 107 Interestingly, prodigiosin ( 29 ), produced most notably by Serratia marcescens, has the additional distinction of being the suspected cause of a medieval-era “miracle”, since bacterial contamination and the subsequent appearance of this deep-red pigment on bread resulted in the initiation of the Feast of Corpus Christi. 108 …”

Section: Compounds From Non-photosynthetic Gram-negative Bacteriamentioning

confidence: 99%

Scrutinizing the Scaffolds of Marine Biosynthetics from Different Source Organisms: Gram-Negative Cultured Bacterial Products Enter Center Stage

et al. 2014

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Compounds from macro marine organisms are presumed to owe their biosynthetic origins to associated microbial symbionts, although few definitive examples exist. An upsurge in the recent literature from 2012 to 2013 has shown that four compounds previously reported from macro marine organisms are in fact biosynthesized by non-photosynthetic Gram-negative bacteria (NPGNB). Structural parallels between compounds isolated from macro marine organisms and NPGNB producers form the basis of this review. Although less attention has been given to investigating the chemistry of NPGNB sources, there exists a significant list of structural parallels between NPGNB and macro marine organism-derived compounds. Alternatively, of the thousands of compounds isolated from Gram-positive actinomycetes, few structural parallels with macro marine organisms are known. A summary of small molecules isolated from marine NPGNB sources is presented, including compounds isolated from marine myxobacteria. From this assemblage of structural parallels and diverse chemical structures, it is hypothesized that the potential for the discovery of inspirational molecules from NPGNB sources is vast and that the recent spike in the literature of macro marine compounds owing their biosynthetic origin to NPGNB producers represents a turning point in the field.

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“…1), were isolated as a 1:1 mixture of methylene homologs (four and six methylene groups) as minor pigments of the marine bacterium Pseudomonas magnesiorubra (Gandhi et al, 1976;Kohl et al, 1974). P. magnesiorubra was originally isolated from the surfaces of the tropical marine green alga Caulerpa peltata.…”

Section: J2 Chemical Studies Of Marine Bacteriamentioning

confidence: 99%